2-(5-(3-nitrobenzoyl)-1,3-dioxoisoindolin-2-yl)acetic acid

ID: ALA607551

PubChem CID: 1364268

Max Phase: Preclinical

Molecular Formula: C17H10N2O7

Molecular Weight: 354.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CN1C(=O)c2ccc(C(=O)c3cccc([N+](=O)[O-])c3)cc2C1=O

Standard InChI:  InChI=1S/C17H10N2O7/c20-14(21)8-18-16(23)12-5-4-10(7-13(12)17(18)24)15(22)9-2-1-3-11(6-9)19(25)26/h1-7H,8H2,(H,20,21)

Standard InChI Key:  CIMHDBDMKDNVCC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   18.8402  -25.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8391  -25.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5539  -26.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5521  -24.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2675  -25.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2723  -25.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0598  -26.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5417  -25.5104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0520  -24.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3023  -24.0586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3193  -26.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3667  -25.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7834  -26.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6084  -26.2127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3751  -26.9345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1257  -24.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1255  -23.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8423  -23.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8424  -22.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1273  -22.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4106  -22.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4140  -23.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6910  -22.2309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9781  -22.6461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6879  -21.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4113  -25.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
  1  2  2  0
 13 15  1  0
  5  4  2  0
  1 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  9 10  2  0
 21 22  2  0
 22 17  1  0
  5  6  1  0
  7 11  2  0
 23 24  2  0
 23 25  1  0
 21 23  1  0
  8 12  1  0
 16 26  2  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA607551

   Cambridge id 5750136

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 354.27

Molecular Weight (Monoisotopic): 354.0488

AlogP: 1.51

#Rotatable Bonds: 5

Polar Surface Area: 134.89

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.47

CX Basic pKa: ┄

CX LogP: 1.79

CX LogD: -1.72

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.37

Np Likeness Score: -1.09

References

1. Fells JI, Tsukahara R, Liu J, Tigyi G, Parrill AL..  (2009)  Structure-based drug design identifies novel LPA3 antagonists.,  17  (21): [PMID:19800804] [10.1016/j.bmc.2009.09.022]

Source

Source(1):

• Scientific Literature